1H-Indazole → HCID 21940669, compound

HRID 2179142Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.I[C:11]1[CH:12]=[C:13]([CH3:18])[CH:14]=[C:15]([CH3:17])[CH:16]=1>>[CH3:18][C:13]1[CH:12]=[C:11]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[N:2]2)[CH:16]=[C:15]([CH3:17])[CH:14]=1

Participants

Reactant 2

HCID 92211H-Indazole

HCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 21940669HCID 21940669, compoundYield 96%

Procedure

Using general procedure A, indazole (148 mg, 1.25 mmol) was coupled with 5-iodo-m-xylene (150 μL, 1.04 mmol). The crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 10:1; 10 mL fractions). Fractions 4-10 provided 222 mg (96% yield) of the product as a pale yellow oil. 1H NMR (300 MHz, CDCl3): δ 8.20 (d, J=1.0 Hz, 1H), 7.83-7.74 (m, 2H), 7.46-7.40 (m, 1H), 7.36 (s, 2H), 7.25-7.19 (m, 1H), 7.01 (s, 1H), 2.43 (s, 6H).

Workup

customThe crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 10:1; 10 mL fractions)

Sources & evidence

ORD record: ord-418f1174de9a4c4ab3254834c1aa08b7
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067955B2

Reaction notes

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